4-Methylmorpholine → HCID 70561853, compound

HRID 1477928Notes

Reaction equation

HRID 1477928 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:11]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)([CH2:17][CH3:18])[CH:12]([OH:16])[CH2:13][O:14][CH3:15].CN1CCOCC1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:11]([N:6]2[C:7]3[C:3](=[C:2]([NH:1][S:34]([CH3:33])(=[O:36])=[O:35])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:5]2)([CH2:17][CH3:18])[CH:12]([OH:16])[CH2:13][O:14][CH3:15])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 86705062HCID 86705062, compound

Product 1

HCID 70561853HCID 70561853, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of the product from Step B (39 mg, 0.108 mmol) and NMM (22 mg, 0.216 mmol) in DCM (8 mL) was added methylsulfonyl chloride (18 mg, 0.163 mmol) dropwise. Then the mixture was stirred at room temperature overnight. The reaction was quenched with saturated ammonium chloride solution, and extracted with ethyl acetate (10 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by PREP-TLC eluting with PE/EA (1/1, v/v) to get the title compound as a colorless amorphous solid. LC/MS m/z=437.1[M+H]+.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate (10 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified
  8. washby PREP-TLC eluting with PE/EA (1/1

Sources & evidence

ORD record
ord-84ee6adbe38d46fd87d9d706a7716803
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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